Synthesis of Cyclobuta[cd]pentalenes via an Intramolecular Double Michael Addition Reaction of 1,3-Cyclopentanedione Derivatives

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-08-10 DOI:10.1021/acs.orglett.5c03049

Makoto Kobayashi, Misora Ono, Tomonari Sasage, Yuma Yamazaki, Takahiro Suzuki, Keiji Tanino, Seiichi Nakamura, Naoki Kanoh and Kazutada Ikeuchi*,

引用次数: 0

Abstract

We describe an intramolecular double Michael addition reaction using 1,3-cyclopentanediones with a Michael acceptor at the C3′ position of the C2 side chain through the formal umpolung of the 1,3-cyclopentanedione moiety. Silylation of the reactants generates 1,4-bis(silyloxy)cyclopentadienes, a silyloxy-substituted carbon which attacks the Michael acceptor to afford bicyclic scaffolds. Appropriate selection of the Michael acceptor induces further cyclization toward the activated cyclopentenone moiety to form a cyclobutane ring, affording cyclobuta[cd]pentalenes.

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1,3-环戊二酮衍生物分子内双迈克尔加成反应合成环丁[cd]五烯

我们描述了一个分子内的双Michael加成反应，利用1,3-环戊二酮和位于C2侧链C3位置的Michael受体，通过对1,3-环戊二酮部分的形式截断。反应物的硅基化反应生成1,4-二（硅氧基）环戊二烯，这是一种硅氧基取代的碳，它攻击迈克尔受体以提供双环支架。适当选择迈克尔受体可诱导活性环戊烯酮部分进一步环化，形成环丁烷环，生成环丁烷[cd]五烯。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.